Anti Markovnikov Addition to An Alkene Chemistry Questions

I’m stuck on a Chemistry question and need an explanation. The prompt for HW6 is attached. Please turn in your solutions as a single, clearly scanned PDF document prepared on separate paper.

CHEM 331 Homework 6 Marshall Fall 2020 Name:

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  1. HBr, specifically, undergoes anti-Markovnikov addition to an alkene in the presence of a radical source like peroxides, but undergoes Markovnikov addition without radicals around. Illustrate this fact by drawing an example alkene, and show curved-arrow mechanisms and products for your alkene reacting under both sets of conditions, including two propagation steps and one termination step for the radical reaction. Explain in a few sentences why the difference in products happens.
  2. It is thermodynamically favorable for bromine to react with alkanes, producing bromoalkanes and HBr as products. However, this reaction essentially doesn’t proceed unless the mixture is irradiated with light. Explain this phenomenon using words, curved-arrow mechanisms, or a combination of the two. Draw an alkane of your choice with at least 8 carbons and draw the major product or products of your alkane reacting with a single equivalent of bromine. That is, draw the major monobromination product(s) of your alkane.
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